During a private trip to Ethiopia in 2015, former U.S. President George W. Bush was met with a delightful surprise.
When he arrived in the ancient Christian town of Lalibela, dozens of children in bright blue Texas Rangers caps, one of the Texan's favorite sports teams, gave him a warm welcome.
“We planned a lot of fun surprises on that trip,” says Jaclyn Sienna India, founder of the luxury lifestyle company Sienna Charles.
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“I try to come up with fun ways to delight travelers, so I bought about 100 Texas Rangers caps. And when Bush arrived in the village, all the kids were wearing them.”
Personal touches, exclusivity, security, privacy: these are the things world leaders have come to expect when they travel.
“It's very much like theater. World leaders have their own vision of what a place could be, how exotic and amazing it is,” India adds. “And we want to bring that vision to life through special moments.”
Bush was not the first world leader India worked with. Her agency has planned more than 100 trips for at least 15 presidents, prime ministers, and senior officials since 2012.
“Whether it's a former president, a billionaire, or a celebrity, each of them is an individual,” she says.
“If you understand what drives them and why they're taking this trip, you'll have a successful relationship.”
Delivering a Tailored Experience
India learned the ins and outs of luxury hospitality at the now-closed Le Bec Fin, then a three-Michelin-star restaurant, where she worked while earning her bachelor's degree in art history at the Tyler School of Art at Temple University in Philadelphia.
“I fell in love with serving ultra-wealthy clients,” she recalls. “I really thrived and understood their needs. That's the heart of my career's success: understanding each person's needs, and then being able to deliver that experience.”
After college, the New York native moved to Palm Beach, Florida, with her then-boyfriend and now-husband Freddy Charles Reinert, where she quickly realized that the level of service in “luxury” travel paled in comparison to fine dining.
“For me, it just didn't make sense. At a restaurant, you could sit for three hours and spend $5,000-10,000,” she recalls.
“You were served by seven people with silverware; the sommelier knew every grape variety and winemaker; the chef came out to your table and knew where the foie gras was sourced.”
At the restaurant, everything was obsessively about service, she says, but in luxury travel that wasn't the case.
“The same category of client was spending $100,000 on a trip to Italy or France, but the travel agent who designed the trip had never even been there,” India says.
Determined to offer a better alternative for affluent travelers, the couple launched Sienna Charles in 2008.
Every trip is tailored to the client's needs, whether it's a multi-generational family getaway in Umbria or a private island in Indonesia.
“I personally vet all of my recommendations, and I'm obsessed with quality and service,” she says.
An Adventure Through Egypt
In 2012, Sienna Charles got its first chance to plan and organize a trip for a world leader.
Approaching India, the client (whose name can't be disclosed due to a non-disclosure agreement) had set their sights on Egypt.
The leader had previously visited the country for work and was “genuinely interested in Egyptology,” India says.
So the travel expert arranged a 12-day, multi-stop adventure that included history and cultural discussions with professionals and academics.
The trip took the world leader from Cairo on a Nile cruise aboard a private yacht, with several stops at historic sites along the way.
They ended the journey in the ancient capital of Luxor, dubbed “the world's largest open-air museum,” where you can find some of the country's oldest tombs and temples.
“We closed the monuments for the leader, and they simply wanted to dive deeper into their personal passion,” India recalls. “They had a romantic notion of the world, where they just couldn't wait to discover this place.”
Thanks to referrals and this first successful trip with a world leader, India went on to plan trips for George W. Bush and several other world leaders.
The Bush Family in Ethiopia
In 2015, India meticulously arranged a trip to the most remote corners of Ethiopia for Bush, his wife Laura, four friends, a personal physician, and 30 Secret Service agents.
Because of the massive entourage, news of the trip leaked.
“We place great importance on confidentiality and privacy,” India says. “But with that many staff and Secret Service agents, it just turned into a media frenzy. Some world leaders travel with just one bodyguard and a baseball cap, and no one knows it's them.”
She says Bush chose Ethiopia because he had been there during his presidency but never had enough time to get out and explore the country more deeply.
“He told me he'd visited about 80 countries during his presidency, but he could be right next to a beautiful landmark like the Taj Mahal and actually see nothing (because of a packed schedule),” India adds.
To immerse the former president in the culture and history, she planned a multi-stage journey from the remote Omo River Valley, home to some of the world's most isolated tribes, in the south, up to Lalibela in the north.
The logistically complex trip required a range of transport, from off-road vehicles to helicopters, private planes, and river boats.
“Lalibela is entirely devoted to Christianity, and it was amazing,” India says, alluding to Bush's religious faith. “When we were in the Omo Valley, the villagers performed a ceremonial dance to welcome him.”
It's All About the Personal Touches
India's team catered to very specific requests around food and drink, because “the trip is entirely about them.”
For example, she says Bush loves comfort food like peanut butter sandwiches and pasta when he travels, so India made sure all of his favorite dishes were available even in the most remote parts of Ethiopia.
“For world leaders, the level of service in their homes is just insane, and they have executive assistants everywhere they go,” she explains. “So when they travel, they really do have high expectations, and that's understandable.”
Since the hotels in Ethiopia didn't meet India's expectations, she worked with local partners to build luxury camps for the former president and his entourage instead.
They purchased brand-new furniture, bedding, and linens, creating beautiful accommodations from scratch.
The great thing about working with world leaders, she says, is that they know how to delegate.
“I tell them what we're thinking, and they let me run with it. These people run countries, so they understand the power of hiring experts and can hand over control to people who are good at what they do,” India says.
On one occasion, she helped a world leader celebrate his wife's birthday by covering the entire floor of a private villa with exotic “Cherry Snow” roses flown in from Ecuador, she says.
Another time, she worked with film-set producers and stylists to create a cinematic Parisian scene in the heart of Miami, where celebrity chef Eric Ripert designed a special menu.
And in Italy, she arranged a private meeting for a world leader with a renowned jewelry designer. The leader helped design a unique gift for his wife: a gold Navette ring with an oval faceted ruby and 24 round-cut diamonds worth $714,000.
Privacy, Security, and Exclusivity
In most cases, India says, her clients come to her with a vision of what they hope to feel on a trip.
Maybe it's a deeper immersion in Chinese culture, poolside relaxation in St. Barts, or simply renting a house and getting to be a grandfather for a week in Italy.
After the initial consultation, India, who has visited more than 80 countries and insists on personally experiencing every recommendation, typically offers three to five options, laying out the pros and cons of each.
From there, the travel expert works closely with the client's chief of staff, personal assistant, and security team to fine-tune the details.
“From room type to food allergies, which restaurants they like, what time they like to wake up, which newspapers they want in their room, which guides they prefer... we account for every detail,” she says.
Transportation usually comes together relatively smoothly, since 100% of her clients have their own private yachts, helicopters, and jets.
As part of the security protocol, Sienna Charles often needs to close down major landmarks and museums so clients can see them in solitude.
“We've closed the Sydney Opera House, Hagia Sophia in Istanbul, the Louvre, Versailles, the Great Sphinx of Giza, Machu Picchu... countless landmarks,” India says. “When you're willing to pay, it's a really simple conversation.”
Usually, Sienna Charles first tries to arrange visits during off-hours. If that's not possible, they'll try making a donation of anywhere from $20,000 to $100,000.
“We don't need to spend money just for the sake of spending money,” she says. “You just need to know who to call. But if they can see it privately, that's a win.”
Leaving Room for Spontaneity
Security is far more complicated, especially when working with world leaders, who typically travel with at least one bodyguard.
“They have a lot of security, and the security wants an itinerary,” she says. “They want it spelled out literally how many steps we need to take from the car to each landmark, to each restaurant.”
At first, this was fairly frustrating for India, because she believes “travel should be spontaneous.”
“The trip unfolds as our clients travel. We figured out pretty quickly after that first trip (to Egypt) that yes, we'll prepare a minute-by-minute report of what we're going to do for security, but we also have to manage the client,” she says. “And if the client feels this is a wonderful trip, that's a win for me.”
That means sometimes you have to deviate from the minute-by-minute itinerary. For example, when she took Bush to Ethiopia, an unexpected opportunity came up to visit a remote tribe in the Omo River Valley.
But the group would have had to descend a very steep path with poor visibility to reach the river, then take a boat to get there.
“I asked his staff if he could do it, so (Bush) could see more. And they said, absolutely not,” India recalls.
“But it would have been the only way to get a moment with this tribe, so I asked Bush directly, and he said, ‘Absolutely.’”
“I've learned to respect the security and staff who want to keep the person safe, but that (strict itinerary) can also keep them from enjoying things,” she says.
A New Era of ‘Out of Control’ Spending
The pandemic didn't affect travel for the ultra-rich and the elite, India says.
“There are plenty of places, like Fiji and Thailand, that started letting private jets in about six months ago,” she says. “It's a great time for ultra-high-net-worth individuals. Because, like everything else, money talks. People are willing to pay to do whatever they want.”
She's noticed a few trends in ultra-luxury travel brought on by the pandemic. For instance, India's clients tend to plan trips at the last minute, sometimes just a day or two before departure, because of the uncertainty around border restrictions and quarantine requirements.
They've also started skipping middlemen entirely, buying their own yachts and private jets, as well as purchasing vacation homes.
What's more, India says privacy has become the norm.
“They don't travel just for the sake of traveling. But when they do go, the wealthy no longer share it online,” she says. “When so many people in the world are struggling, they're not going to post photos on their mega-yacht.”
Even so, the money being spent on trips right now is “insane,” she adds. “People just want what they want. If they rent a yacht, it's going to be the most expensive yacht. And they don't deal with staff who don't know how to handle them.”
Before the pandemic, India helped clients rent yachts for roughly $200,000-300,000 a week. Now they're booking boats that cost up to $1 million a week.
When it comes to vacation homes and estates, costs have jumped from an average of $10,000 a night to $35,000 or more for Sienna Charles clients.
“Spending has definitely gotten out of control,” India says. “It's everywhere. People are simply willing to pay for exclusivity and being in the right place at the right time. Always.”
